Ethyl bromoacetate → Ethyl N-((pyridin-2-yl)methyl)glycinate

HRID 1974921Notes

Reaction equation

HRID 1974921 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O>[CH2:20]([O:19][C:17]([CH2:16][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 195092-Pyridinemethanamine

Product 1

HCID 13236080Ethyl N-((pyridin-2-yl)methyl)glycinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Finely powdered potassium carbonate (5.8 g) was suspended in a solution of 2-(aminomethyl)pyridine (3.0 g) and ethyl bromoacetate (3.1 ml) in dimethylformamide (30 ml). The mixture was stirred at room temperature overnight, then poured into ice water. The mixture was extracted with ethyl acetate (50 ml×2) and the organic layer was washed with saturated sodium chloride solution (2 times), dried over magnesium sulfate, and evaporated in vacuo. The residue was purified with a silica gel column chromatography (MeOH:CHCl3 =1:99 as an eluent) to give N-(ethoxycarbonylmethyl)-N-(pyridin-2-ylmethyl)amine (2.30 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (50 ml×2)
  2. washthe organic layer was washed with saturated sodium chloride solution (2 times)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified with a silica gel column chromatography (MeOH

Sources & evidence

ORD record
ord-e0075a6ff27447b6b58ab99230b7b231
Source dataset
uspto-grants-1994_02
Patent number
US05284828

Reaction notes

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